Photo-decomposable compound, photoresist composition including the same, and method of manufacturing integrated circuit device

Abstract

A photo-decomposable compound, a photoresist composition, and a method of manufacturing an IC device, the compound generating acid upon exposure and acts as a quenching base that neutralizes acid in an unexposed state and being represented by Formula 1:wherein, in Formula 1, Ra is a C5 to C40 substituted or unsubstituted cyclic hydrocarbon group including at least one nitrogen atom, Ya is a C1 to C20 divalent linear or cyclic hydrocarbon group, n is an integer of 1 to 5, and A+ is a counter ion.

What is claimed is: 
     
       1. A photo-decomposable compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         Y a  is a C1 to C20 divalent linear or cyclic hydrocarbon group, 
         n is an integer of 1 to 5, 
         A +  is a counter ion, 
         R a  is one of the following groups: 
       
       
         
           
           
               
               
           
         
         in which -* indicates a bond to the oxygen of Formula 1. 
       
     
     
       2. The photo-decomposable compound as claimed in  claim 1 , wherein Y a  is a C1 to C5 substituted or unsubstituted alkylene group, a C5 to C20 divalent monocyclic or condensed alicyclic hydrocarbon group, or a C5 to C20 divalent monocyclic or condensed aromatic hydrocarbon group. 
     
     
       3. The photo-decomposable compound as claimed in  claim 1 , wherein:
 Y a  is —(CH 2 ) m —, and 
 m is an integer of 1 to 5. 
 
     
     
       4. The photo-decomposable compound as claimed in  claim 1 , wherein:
 Y a  is one of the following groups: 
 
       
         
           
           
               
               
           
         
         -* is a bond to the carbonyl carbon or the fluorinated carbon of Formula 1, 
         r is an integer of 0 to 2, and 
         each of R Y1 , R Y2 , R Y3 , and R Y4  is independently a C1 to C10 linear or branched alkyl group, a cyclopropyl group, a cyclopentyl group, or a cyclohexyl group. 
       
     
     
       5. The photo-decomposable compound as claimed in  claim 1 , wherein A +  is a sulfonium cation, an iodonium cation, or an ammonium cation. 
     
     
       6. The photo-decomposable compound as claimed in  claim 1 , wherein the compound generates acid having an acid dissociation constant of 1 to 10. 
     
     
       7. A photoresist composition, comprising:
 a chemically amplified polymer; 
 a photoacid generator; 
 a photo-decomposable compound; and 
 a solvent, 
 wherein the photo-decomposable compound is represented by Formula 1: 
 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         Y a  is a C1 to C20 divalent linear or cyclic hydrocarbon group, 
         n is an integer of 1 to 5, and 
         A +  is a counter ion, 
         R a  is one of the following groups: 
       
       
         
           
           
               
               
           
         
         in which -* indicates a bond to the oxygen of Formula 1. 
       
     
     
       8. The photoresist composition as claimed in  claim 7 , wherein:
 the photoacid generator generates a first acid having a first acid dissociation constant, 
 the photo-decomposable compound generates a second acid having a second acid dissociation constant, and 
 the second acid dissociation constant is higher than the first acid dissociation constant. 
 
     
     
       9. The photoresist composition as claimed in  claim 7 , wherein:
 Y a  is a divalent group represented by —(CH 2 ) m —, and 
 m is an integer of 1 to 5. 
 
     
     
       10. A method of manufacturing an integrated circuit device, the method comprising:
 providing a substrate that includes a feature layer; 
 forming a photoresist film on the feature layer, the photoresist film including a chemically amplified polymer, a photoacid generator, and the photo-decomposable compound as claimed in  claim 1 ; 
 exposing a first area of the photoresist film to generate a first acid and a second acid in the first area of the photoresist film, wherein the first area is a portion of the photoresist film, the first acid is derived from the photoacid generator, and the second acid is derived from the photo-decomposable compound; 
 deprotecting an acid-labile group included in the chemically amplified polymer by using the first acid and the second acid in the exposed first area of the photoresist film; 
 removing the exposed first area of the photoresist film by using a developer to form a photoresist pattern comprising a non-exposed area of the photoresist film; and 
 processing the feature layer using the photoresist pattern. 
 
     
     
       11. The method as claimed in  claim 10 , wherein:
 forming the photoresist film includes coating the feature layer with a photoresist composition, and 
 the photoresist composition includes the chemically amplified polymer, the photoacid generator, the photo-decomposable compound, and a solvent. 
 
     
     
       12. The method as claimed in  claim 10 , wherein the photo-decomposable compound is represented by Formula 1a, in which R a  is defined the same as that of Formula 1: 
       
         
           
           
               
               
           
         
       
     
     
       13. The method as claimed in  claim 10 , wherein:
 during the exposing of the first area of the photoresist film, the first acid has a first acid dissociation constant, and the second acid has a second acid dissociation constant, and 
 the second acid dissociation constant is higher than the first acid dissociation constant. 
 
     
     
       14. The method as claimed in  claim 10 , wherein exposing the first area of the photoresist film includes exposing the first area using an extreme ultraviolet laser.